Water → HCID 68775704, compound

HRID 2263218Notes

Reaction equation

[C:1]([NH:4][C:5]1[N:10]=[CH:9][C:8]([NH:11][C:12](=[O:19])OCC(F)(F)F)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[F:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[N:28]=[C:29]([CH:32]3[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]3)[S:30][CH:31]=2)=[CH:23][CH:22]=1.C(N(C(C)C)CC)(C)C.O>CS(C)=O>[C:1]([NH:4][C:5]1[N:10]=[CH:9][C:8]([NH:11][C:12]([N:35]2[CH2:34][CH2:33][CH:32]([C:29]3[S:30][CH:31]=[C:27]([C:24]4[CH:23]=[CH:22][C:21]([F:20])=[CH:26][CH:25]=4)[N:28]=3)[CH2:37][CH2:36]2)=[O:19])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 2,2,2-trifluoroethyl [6-(acetylamino)pyridin-3-yl]carbamate (274 mg, 0.839 mmol), 4-[4-(4-fluorophenyl)-1,3-thiazol-2-yl]piperidine (200 mg, 0.762 mmol) and diisopropylethylamine (0.266 ml, 1.52 mmol) in dimethylsulfoxide (2.5 ml) was stirred at 70° C. for 12 hours. Water was poured into the reaction solution, and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was recrystallized from a mixed solvent of hexane and tetrahydrofuran to give the desired product (193 mg, 57.6%) as a solid.

Workup

extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with water
dry with materialdried over anhydrous magnesium sulfate
distillationthe solvent was distilled off under reduced pressure
customThe residue was recrystallized from a mixed solvent of hexane and tetrahydrofuran

Sources & evidence

ORD record: ord-d0809ead93774d19a91d81c85a8ba7b7
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07851473B2

Reaction notes

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